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You Asked: Is He Off Limits?

Dear Sugar,

My ex-boyfriend and I have been broken up for six years now, but we remain very good friends. I have always had a little crush on his roommate, and just recently we talked about the possibility of taking our relationship to the next level. My ex and I have both dated other people since our split, but is dating his best friend and roommate just totally not allowed? Should I wait until he eventually moves out? — Proceeding Cautiously Cassie

To see DearSugar's answer

Dear Proceeding Cautiously Cassie,

Six years is a long time to be broken up with your ex, and while I think it's great that you remain good friends, I think it's high time you move on with your life. Dating his best friend might be a little too close for comfort, but who knows, he might be totally OK with the idea! Before taking this friendship to the next level, I'd talk to your ex about it first and find out where he stands. If he's all for it, great, but if he's opposed, you're going to have to ask yourself which relationship is more important to you. I hope it works out for everyone involved, and good luck to you!


Join The Conversation
kristyy kristyy 8 years
The best friend should talk to him, not you. You're his ex, and even if you are on good terms and still friends, the other guys is his BEST friend. It's better for him to hear it from his best friend. If he says no, then the best friend will have to decide which relationship is more important to him. Unfortunately, it may mean their friendship is more important.
sparklestar sparklestar 8 years
I'm dating my ex's best friend! I should have always gotten together with the best friend but it happened I met my ex first. :( Meeting my ex led me to his best friend though and we are way better suited for each other. ;) I would just go for it! Why on earth not?!
sarah-bee sarah-bee 8 years
You really should talk to your ex before moving forward not so much to get his permission but more so to prevent any hurt feelings. If you're truly friends he's unlikely to object but consulting him before dating his best friend rather than telling him after the fact will keep him from feeling like he's been left out of the loop. It will also mean that neither you nor your ex's friend will be worrying about what your ex may be feeling which is the kind of baggage that could bring any new relationship down.
defygrav12 defygrav12 8 years
Maybe talk to your ex first, just to pay him respect as a friend, but girl, you have been broken up for SIX YEARS. Holy cow. Go for it. :)
dm8bri dm8bri 8 years
Since you and your ex are still good friends and he lives with your potential boyfriend, I think it's only fair that the ex be consulted before going forward. However, I think his roommate/best friend/your love interest should be the one to ask. Despite the fact that you are still close to your ex, the roommate is probably closer, and if he's that interested in you he should man up and show it.
GScott86 GScott86 8 years
You shouldn't have to ask your ex for anything, and you shouldn't have to worry about your ex knowing much about your personal life if you don't want him to. Why not just walk the other direction away from both of these. Sounds like a ticket to dramaland to me. But hey, if you want his roommate, go for it. Just realize your ex might be all up in your face and business and may or may not cause trouble for you two. May get annoying so be prepared for that.
notinthemood notinthemood 8 years
I think it sounds incredibly awkward. You don't need permission, but I wouldn't want to be in that situation. If it doesn't bother you, I guess it doesn't matter.
vmruby vmruby 8 years're entitled to be happy and if he's the one then I think you should go for it. It's been 6 years and life has gone on for everyone. There's no plausible reason as far as I can see that you should have to pass it by your ex first for approval before you start a relationship with his roommate.IMO it's no longer his business who you date.....
kurniakasih kurniakasih 8 years
It's not a 'fresh' break up (6 years ago and everyone has moved on) and I don't think you should be asking permission from ANYONE regarding whom you want to ask (esp. if you're an adult). Although there's a possibility that things can get awkward. But how does HIS best friend feel about this anyway. You're not your ex's bff, but his friend is (and roommate too, to boot). If he wants to date you, he should at least bring this up first to his bff not you. You can go talk to him (your ex) after you and the new guy are sure that you guys are going to date.
Chrstne Chrstne 8 years
They are best friends, but you've been ex's for 6 years. It really shouldn't matter at that point. I think that's just standard immediate future after the break up" procedure to not date your ex's friend. But it's 6 years down the road...certainly not fresh.
Chrstne Chrstne 8 years
I think I'm the only one who thinks it's no business of your friends who you date. It's not like you're dating your girl friends ex boyfriend -- your dating your friend's roomie! I understand he's your ex and whatnot, and I understand you're friends...but why would it matter if you dated his roommate? That's not like some off limits territory. And if it's too close for comfort for him, then it doesn't matter -- it's not as if your his girlfriend or a friend that is entitled to choose for you. You can have both your friend and a boyfriend. I wouldn't ask your ex, I'd say that you and his roommate have really hit it off, and think it may be going to the next level, and then feel it out. If he has something to say about it, listen. Maybe approach it with "I don't know how you'll feel about this, but I hope you can be accepting" and tell him the above. Don't just straight up ask "Can I date your roommate?"
KAT0002 KAT0002 8 years
i would say ask your ex first.
KadBunny KadBunny 8 years
Yeah, talk to him first. After that it wouldn't matter what you do, in my opinion. It's been long enough. Even if he says no at least you were respectful enough to ask him. But I guess like Dear said: if it comes to that point it'll just be a matter of which relationship is more important to you. Though I do hope he won't get in the way of this new one. :( Good luck!
sarahcateh sarahcateh 8 years
I'd say ask your ex first, and then go from there. If he says yes, you're in the clear. If he says no, talk to your guy about how the two of you want to proceed.
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